This invention relates to certain sulfonylurea compounds having a ring structure ortho to the sulfonyl bridge, agricultural compositions thereof and a method of use as general preemergence and/or postemergence herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides which will control all plant growth are desired. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,368,069 discloses herbicidal sulfonylureas of the formula ##STR1## wherein R is ##STR2## R.sub.2 is C.sub.2 -C.sub.5 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl or C.sub.2 -C.sub.3 alkenyl substituted with 1-3 Cl;
n is 0 or 1; PA1 R.sub.1 is, inter alia, H, F, Cl, Br; PA1 R.sub.5 and R.sub.6 are independently H or CH.sub.3 ; etc. PA1 R.sub.9 is OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.2 is H, F, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.3 is H or CH.sub.3 ; etc. PA1 W is O or S; PA1 R.sub.1 is H, F, Cl, Br, CH.sub.3, CF.sub.3 or OCH.sub.3 ; PA1 R.sub.13 is H or CH.sub.3 ; etc. PA1 G is 0 or 2; PA1 T is O or .dbd.NOR.sub.1.sup.III ; PA1 R.sub.2 is, inter alia, H, F, Cl, Br or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 is H, F, Cl, Br or CH.sub.3. PA1 R.sub.2 is, inter alia, H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; PA1 R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by one or more fluorine or bromine atoms or by one or more hydroxyl, cyano, nitro, --(Y).sub.m CO(Z).sub.n R.sub.8, --SO.sub.2 NR.sub.11 R.sub.12, --S(O).sub.p --C.sub.1 -C.sub.3 haloalkyl or --S(O).sub.n --C.sub.1 -C.sub.3 alkyl groups, and which may additionally be substituted by one or more chlorine atoms; PA1 X is O or S; PA1 R.sub.6 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; etc. PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sub.c, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3 or CH.sub.2 CN; PA1 R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.a and R.sub.b may be taken together as (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5 or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, phenyl, phenyl substituted with Cl, NO.sub.2, CH.sub.3 or OCH.sub.3, C.sub.1 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkylsulfonyl or di(C.sub.1 -C.sub.2)alkylamino sulfamoyl; PA1 Q is ##STR11## n is 0, 1 or 2; R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA1 R.sub.10 is H or C.sub.1 -C.sub.4 alkyl; PA1 E is a bridge of 4 or 5 atoms, which may be substituted or unsubstituted, containing 0-2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and also containing 2-5 carbon atoms, said bridge together with one carbon attachment site forming a partially saturated or a fully unsaturated, nonaromatic 5- or 6-membered carbocyclic or heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, they must be separated by at least one atom of carbon, and that oxygen and sulfur are only linked to each other if the sulfur is in the form SO or SO.sub.2 ; in the bridging group E, sulfur may take the form of S, SO or SO.sub.2 and one or two of the carbon atoms may be a carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof; when one of the bridging atoms is a substituted carbon, the substituents on said carbon include H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, or C.sub.1 -C.sub.4 haloalkoxy; when the bridging atom is a nitrogen, the substituent on said nitrogen includes H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA1 A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, ##STR13## W.sub.1 and W.sub.2 are independently O or S; m is 2 or 3; PA1 R.sub.d is H or CH.sub.3 ; PA1 R.sub.e is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.f is C.sub.1 -C.sub.2 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR14## (b) when X is Cl, Br, F or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H or N(OCH.sub.3)CH.sub.3 ; PA1 (c) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (d) when the bridging group E contains a thiocarbonyl substituent, said thiocarbonyl carbon must be bonded to a nitrogen atom; PA1 (e) when J is J-2 or J-3, the substituent Q and the sulfonylurea bridge are on adjacent carbon atoms; PA1 (f) when the total number of carbon atoms in X and Y is greater than 4, then the total number of carbon atoms in R.sub.1, R.sub.2 and Q is less than or equal to 10; and PA1 (g) X.sub.4 and Y.sub.4 are not simultaneously Cl. PA1 R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently H or C.sub.1 -C.sub.4 alkyl and R.sub.10 is H or CH.sub.3 ; PA1 provided that the total number of carbon atoms of R.sub.4, R.sub.5, R.sub.7, R.sub.8 and R.sub.9 is less than or equal to 4. PA1 (2) Compounds of Preferred 1 where X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, Br, F, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5, cyclopropyl, ##STR16## OCF.sub.2 H, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3. (3) Compounds of Preferred 2 where R.sub.1 is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio. PA1 (4) Compounds of Preferred 3 where R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently H or CH.sub.3 ; R.sub.3 is H or C.sub.1 -C.sub.2 alkyl; and R.sub.2 is H, C.sub.1 -C.sub.2 alkyl or CH.sub.2 CH.dbd.CH.sub.2. PA1 (5) Compounds of Preferred 4 where A is A-1; X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2 ; and Z is CH or N. PA1 (6) Compounds of Preferred 5 where J is J-1 and R.sub.1 is in the 5-position. PA1 (7) Compounds of Preferred 5 where J is J-2 and R.sub.1 is H. PA1 (8) Compounds of Preferred 5 where J is J-3 and R.sub.1 is H. PA1 (9) Compounds of Preferred 5 where J is J-4 and R.sub.1 is H. PA1 (10) Compounds of Preferred 5 where J is J-5 and R.sub.1 is H. PA1 (11) Compounds of Preferred 6 where Q is Q-1. PA1 (12) Compounds of Preferred 6 where Q is Q-2. PA1 (13) Compounds of Preferred 6 where Q is Q-3. PA1 (14) Compounds of Preferred 6 where Q is Q-4. PA1 (15) Compounds of Preferred 6 where Q is Q-5. PA1 (16) Compounds of Preferred 6 where Q is Q-6. PA1 (17) Compounds of Preferred 6 where Q is Q-7. PA1 (18) Compounds of Preferred 6 where Q is Q-8. PA1 (19) Compounds of Preferred 6 where Q is Q-9. PA1 (20) Compounds of Preferred 6 where Q is Q-10. PA1 (21) Compounds of Preferred 6 where Q is Q-11. PA1 (22) Compounds of Preferred 6 where Q is Q-12. PA1 (23) Compounds of Preferred 6 where Q is Q-13. PA1 (24) Compounds of Preferred 6 where Q is Q-14. PA1 (25) Compounds of Preferred 6 where Q is Q-15. PA1 (26) Compounds of Preferred 6 where Q is Q-16. PA1 (27) Compounds of Preferred 6 where Q is Q-17. PA1 (28) Compounds of Preferred 6 where Q is Q-18. PA1 (29) Compounds of Preferred 6 where Q is Q-19. PA1 (30) Compounds of Preferred 6 where Q is Q-20. PA1 (31) Compounds of Preferred 6 where Q is Q-21. PA1 (32) Compounds of preferred 6 where Q is Q-22. PA1 (33) Compounds of Preferred 6 where Q is Q-23. PA1 (34) Compounds of Preferred 6 where Q is Q-24. PA1 (35) Compounds of Preferred 6 where Q is Q-25. PA1 (36) Compounds of Preferred 6 where Q is Q-26. PA1 (37) Compounds of Preferred 6 where Q is Q-27. PA1 (38) Compounds of Preferred 6 where Q is Q-28. PA1 (39) Compounds of Preferred 6 where Q is Q-29. PA1 (40) Compounds of Preferred 6 where Q is Q-30. PA1 (41) Compounds of Preferred 6 where Q is Q-31. PA1 (42) Compounds of Preferred 6 where Q is Q-32. PA1 (43) Compounds of Preferred 6 where Q is Q-33. PA1 (44) Compounds of Preferred 6 where Q is Q-34. PA1 (45) Compounds of Preferred 6 where Q is Q-35. PA1 (46) Compounds of Preferred 6 where Q is Q-36. PA1 (47) Compounds of Preferred 6 where Q is Q-37. PA1 (48) Compounds of Preferred 6 where Q is Q-38. PA1 (49) Compounds of Preferred 6 where Q is Q-39. PA1 (50) Compounds of Preferred 6 where Q is Q-40. PA1 (51) Compounds of Preferred 6 where Q is Q-41. PA1 (52) Compounds of Preferred 6 where Q is Q-42. PA1 (53) Compounds of Preferred 6 where Q is Q-43. PA1 (54) Compounds of Preferred 6 where Q is Q-44. PA1 (55) Compounds of Preferred 6 where Q is Q-45. PA1 (56) Compounds of Preferred 6 where Q is Q-46. PA1 (57) Compounds of Preferred 6 where Q is Q-47. PA1 (58) Compounds of Preferred 6 where Q is Q-48. PA1 (59) Compounds of Preferred 6 where Q is Q-49. PA1 (60) Compounds of Preferred 6 where Q is Q-50. PA1 (61) Compounds of Preferred 6 where Q is Q-51. PA1 (62) Compounds of Preferred 6 where Q is Q-52. PA1 (63) Compounds of Preferred 6 where Q is Q-53. PA1 (64) Compounds of Preferred 6 where Q is Q-54. PA1 (65) Compounds of Preferred 6 where Q is Q-55. PA1 (66) Compounds of Preferred 6 where Q is Q-56. PA1 (67) Compounds of Preferred 6 where Q is Q-57. PA1 (68) Compounds of Preferred 6 where Q is Q-58. PA1 (69) Compounds of Preferred 6 where Q is Q-59. PA1 (70) Compounds of Preferred 6 where Q is Q-60. PA1 (71) Compounds of Preferred 6 where Q is Q-61. PA1 (72) Compounds of Preferred 6 where Q is Q-62. PA1 (73) Compounds of Preferred 6 where Q is Q-63. PA1 (74) Compounds of Preferred 6 where Q is Q-64. PA1 (75) Compounds of Preferred 6 where Q is Q-65. PA1 (76) Compounds of Preferred 6 where Q is Q-66. PA1 (77) Compounds of Preferred 6 where Q is Q-67. PA1 (78) Compounds of Preferred 6 where Q is Q-68. PA1 (79) Compounds of Preferred 6 where Q is Q-69. PA1 (80) Compounds of Preferred 6 where Q is Q-70. PA1 (81) Compounds of Preferred 6 where Q is Q-71. PA1 (82) Compounds of Preferred 6 where Q is Q-72. PA1 (83) Compounds of Preferred 6 where Q is Q-73. PA1 (84) Compounds of Preferred 6 where Q is Q-74. PA1 (85) Compounds of Preferred 6 where Q is Q-75. PA1 (86) Compounds of Preferred 6 where Q is Q-76. PA1 (87) Compounds of Preferred 6 where Q is Q-77. PA1 (88) Compounds of Preferred 6 where Q is Q-78. PA1 (89) Compounds of Preferred 6 where Q is Q-79. PA1 (90) Compounds of Preferred 6 where Q is Q-80. PA1 (91) Compounds of Preferred 11 where W.sub.3 is O. PA1 (92) Compounds of Preferred 15 where W.sub.3 is NH or NCH.sub.3. PA1 (93) Compounds of Preferred 17 where W.sub.4 is S or SO.sub.2. PA1 (94) Compounds of Preferred 18 where W.sub.4 is S or SO.sub.2. PA1 (95) Compounds of Preferred 26 where W.sub.3 is O. PA1 (96) Compounds of Preferred 32 where W.sub.3 is NH or NCH.sub.3. PA1 (97) Compounds of Preferred 35 where W.sub.4 is S or SO.sub.2. PA1 (98) Compounds of Preferred 36 where W.sub.4 is S or SO.sub.2. PA1 (99) Compounds of Preferred 65 where W.sub.3 is O. PA1 (100) Compounds of Preferred 71 where W.sub.3 is NH or NCH.sub.3. PA1 (101) Compounds of Preferred 72 where W.sub.3 is NH or NCH.sub.3. PA1 (102) Compounds of Preferred 86 where W.sub.3 is O. PA1 (103) Compounds of Preferred 87 where W.sub.3 is O. PA1 Br can be replaced by Cl or I. PA1 R.sub.3 is C.sub.1 -C.sub.4 alkyl. PA1 R.sub.3 is as defined above. PA1 R.sub.3 is H or C.sub.1 -C.sub.4 alkyl; and PA1 n is 1 or 2. PA1 R.sub.3 is H. PA1 B is Br, NO.sub.2, SR.sub.12 ; PA1 R.sub.12 is C.sub.2 -C.sub.4 alkyl or benzyl; and PA1 R.sub.1 is as previously defined.
European Patent Application (EP-A) No. 106,512, published Apr. 25, 1984, discloses herbicidal sulfonylureas of the formula ##STR3## wherein R.sub.1 is, in part, CH.dbd.CBr.sub.2, CH.dbd.CHCO.sub.2 CH.sub.3, CH.dbd.CF.sub.2 or CH.dbd.CHR.sub.9 ;
U.S. Pat. No. 4,460,401 discloses herbicidal sulfonylureas of the formula ##STR4## where, in part, Q is an optionally substituted ring such as ##STR5## etc; W' is O or S;
U.S. Pat. No. 4,370,480 discloses herbicidal sulfonylureas of the formula ##STR6## where, in part, R.sub.1 is ##STR7## R is H, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.6 alkenyl, etc.; B is O or S(O).sub.G ;
South African Patent Application No. 83/6449, published Mar. 1, 1984, discloses herbicidal sulfonylureas of the formula ##STR8## wherein R.sub.1 is H, halogen, NO.sub.2, NH.sub.2, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 haloalkyl or a QR.sub.7, CO.sub.2 R.sub.8 or --(CO).sub.n NR.sub.9 R.sub.10 radical;